title: Ralfuranone thioether production by the plant pathogen Ralstonia solanacearum.
abstract: Ralfuranones are aryl-substituted furanone secondary metabolites of the Gram-negative plant pathogen Ralstonia solanacearum. New sulfur-containing ralfuranone derivatives were identified, including the methyl thioether-containing ralfuranone D. Isotopic labeling in vivo, as well as headspace analyses of volatiles from R. solanacearum liquid cultures, established a mechanism for the transfer of an intact methylthio group from L-methionine or α-keto-γ-methylthiobutyric acid. The methylthio acceptor molecule ralfuranone I, a previously postulated biosynthetic intermediate in ralfuranone biosynthesis, was isolated and characterized by NMR. The highly reactive Michael acceptor system of this intermediate readily reacts with various thiols, including glutathione.
authors.affiliation: Friedrich-Schiller-Universität, Department of Pharmaceutical Biology at the Hans-Knöll-Institut, Beutenbergstrasse 11a, 07745 Jena (Germany).
authors.forename: Julia
authors.initials: J
authors.lastname: Pauly
authors.forename: Dieter
authors.initials: D
authors.lastname: Spiteller
authors.forename: Jeanine
authors.initials: J
authors.lastname: Linz
authors.forename: Jonathan
authors.initials: J
authors.lastname: Jacobs
authors.forename: Caitilyn
authors.initials: C
authors.lastname: Allen
authors.forename: Markus
authors.initials: M
authors.lastname: Nett
authors.forename: Dirk
authors.initials: D
authors.lastname: Hoffmeister
mesh_terms: D001426:Bacterial Proteins / Q000235:genetics / Q000378:metabolism; D005663:Furans / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D055785:Gene Knockdown Techniques; D007553:Isotope Labeling; D010957:Plasmids / Q000378:metabolism; D043368:Ralstonia solanacearum / Q000737:chemistry* / Q000378:metabolism; D013440:Sulfides / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry / Q000378:metabolism; D055549:Volatile Organic Compounds / Q000737:chemistry / Q000378:metabolism
chemical_list: D001426:Bacterial Proteins; D005663:Furans; D013440:Sulfides; D055549:Volatile Organic Compounds; D013455:Sulfur
keywords: Ralstonia solanacearum; biosynthesis; natural products; ralfuranones; thioethers